Potassium Carbonate → HCID 70979895, compound

HRID 1475382Notes

Reaction equation

HRID 1475382 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[CH:15]=[C:14](Cl)[N:13]=[CH:12][C:11]=2[C:10]([CH3:19])([CH3:18])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:20]1(B(O)O)[CH2:24][CH2:23][CH2:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.CC1C=CC=CC=1[P](C1C=CC=CC=1C)([Pd](Cl)(Cl)[P](C1=C(C)C=CC=C1)(C1C=CC=CC=1C)C1C=CC=CC=1C)C1C=CC=CC=1C>[C:1]([O:5][C:6]([N:8]1[C:16]2[CH:15]=[C:14]([C:20]3[CH2:24][CH2:23][CH2:22][CH:21]=3)[N:13]=[CH:12][C:11]=2[C:10]([CH3:19])([CH3:18])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 3861343(Cyclopent-1-en-1-yl)boronic acidHCID 86723969tert-Butyl 6-chloro-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-c]pyridine-1-carboxylate

Product 1

HCID 70979895HCID 70979895, compoundYield 57%

Reagents, catalysts & solvents 3

HCID 178424406HCID 178424406, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 6-chloro-3,3-dimethyl-2,3-dihydro-pyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl ester (340 mg, 1.2 mmol), cyclopenten-1-ylboronic acid (270 mg, 2.4 mmol), potassium carbonate (414 mg, 3.0 mmol) and dichlorobis(tri-o-tolyl-phosphine)palladium(II) (38 mg, 0.04 mmol) in 1,4-dioxane (6 mL) and water (1.5 mL) was degassed and heated in a reaction vial at 90° C. for 2 h. The reaction mixture was cooled, water (20 mL) was added and the product was extracted with EtOAc (2×20 mL). The combined organic layers were dried, filtered and the solvent evaporated. The crude material was purified by column chromatography (SiO2, petrol-EtOAc 0-60%) to afford the title compound (213 mg, 57%). MS: [M+H]+=315.

Workup

  1. customwas degassed
  2. temperatureThe reaction mixture was cooled
  3. additionwater (20 mL) was added
  4. extractionthe product was extracted with EtOAc (2×20 mL)
  5. customThe combined organic layers were dried
  6. filtrationfiltered
  7. customthe solvent evaporated
  8. customThe crude material was purified by column chromatography (SiO2, petrol-EtOAc 0-60%)

Sources & evidence

ORD record
ord-602bc2e0e4e34c4bbf29e0b4ef26a9a7
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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